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Puerto Rico Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in October 2026 or 2027, we have 23 unique cruise itineraries and 128 departures available, operated by seven of the world's leading cruise lines departing in October.
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23 Cruises (128 Cruise Departures)
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,502
Oceanview
$1,615
Balcony
$1,734
Suite
$2,910
From
US$1,502
Save 888
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$634
Oceanview
$774
Balcony
$799
Suite
$1,299
From
US$634
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise
 (5)

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 23 October 2026
Visit: Spain, Portugal, Sint Maarten, Puerto Rico
Viking $999 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,299
Suite
$5,999
From
US$3,299
Save 200
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Mar 2026 to Oct 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$971
Oceanview
$1,028
Balcony
$1,156
Suite
$2,845
From
US$971
Save 749
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,301
Oceanview
$1,597
Balcony
$1,584
Suite
$2,809
From
US$1,301
Save 618
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$574
Oceanview
$734
Balcony
$914
Suite
$1,434
From
US$574
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$1,052
Oceanview
$1,256
Balcony
$1,480
Suite
-
From
US$1,052
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,261
Oceanview
$1,451
Balcony
$1,561
Suite
$3,312
From
US$1,261
Save 939
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$912
Oceanview
$1,094
Balcony
$1,323
Suite
$5,155
From
US$912
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$486
Oceanview
$516
Balcony
$631
Suite
$811
From
US$486
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$973
Oceanview
$1,165
Balcony
$1,394
Suite
$2,736
From
US$973
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$777
Oceanview
$1,087
Balcony
$1,380
Suite
$2,185
From
US$777
Save 481
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,789
Oceanview
$2,059
Balcony
$2,499
Suite
$4,342
From
US$1,789
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$1,214
Oceanview
$1,444
Balcony
$1,704
Suite
$6,545
From
US$1,214
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$510
Oceanview
$540
Balcony
$1,293
Suite
$1,367
From
US$510
Save 331
Per Person
View Trip
8 Day Valiant's Haunted Halloween Soiree with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
-
Oceanview
$1,183
Balcony
$1,438
Suite
$4,053
From
US$1,183
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$1,211
Oceanview
$1,470
Balcony
$1,747
Suite
$6,804
From
US$1,211
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$674
Oceanview
-
Balcony
$749
Suite
$1,029
From
US$674
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,423
From
US$689
Save 568
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,054
Oceanview
$1,104
Balcony
$1,354
Suite
$3,885
From
US$1,505
Save 25
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$986
Oceanview
$1,176
Balcony
$1,526
Suite
$2,126
From
US$986
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Bonus Onboard Credit
Inside
$1,400
Oceanview
$1,600
Balcony
$1,970
Suite
$3,446
From
US$1,400
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Bonus Onboard Credit
Inside
$1,109
Oceanview
$1,339
Balcony
$1,568
Suite
-
From
US$1,109
Per Person
View Trip
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